Nitrogen → 2-(5-Acetyl-thiophen-2-ylmethyl)-thiazole-4-carboxylic acid

HRID 1189420Notes

Reaction equation

HRID 1189420 reaction equation
N#N.C([O:5][C:6]([C:8]1[N:9]=[C:10]([CH2:13][C:14]2[S:15][C:16]([C:19](=[O:21])[CH3:20])=[CH:17][CH:18]=2)[S:11][CH:12]=1)=[O:7])C.[OH-].[Na+]>C1COCC1.Cl>[C:19]([C:16]1[S:15][C:14]([CH2:13][C:10]2[S:11][CH:12]=[C:8]([C:6]([OH:7])=[O:5])[N:9]=2)=[CH:18][CH:17]=1)(=[O:21])[CH3:20]

Participants

6

Reactant 3

HCID 947NitrogenHCID 14798Sodium HydroxideHCID 671284092-(5-Acetyl-thiophen-2-ylmethyl)-thiazole-4-carboxylic acid ethyl ester

Product 1

HCID 671284532-(5-Acetyl-thiophen-2-ylmethyl)-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-(5-acetyl-thiophen-2-ylmethyl)-thiazole-4-carboxylic acid ethyl ester (2.20 g, 7.46 mmol) in THF (32 mL) was treated at rt with 1N NaOH (16 mL, 16.00 mmol) and the reaction mixture was stirred for 16 h at rt. The reaction mixture was poured in 1N HCl and extracted twice with EA. The combined org. extracts were dried over MgSO4, filtered, and the solvent was removed under reduced pressure to give the title compound as a deep brown foam. LC-MS-conditions 02: tR=0.78 min, [M+H]+=268.08.

Workup

  1. extractionextracted twice with EA
  2. dry with materialextracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6316ff01daf84f6ba3e566da4dcc6a5f
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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